Synthesis of 6-dialkylaminoalkylamino pyrano[2,3-c]acridones and benzo[b]pyrano[3,2-h]acridones: soluble acronycine analogues with increased cytotoxic activity

Oncol Res. 2003;13(4):191-7.

Abstract

The novel 6-dialkylaminoalkylamino-3,3,12-trimethyl-3,12-dihydro-7H-pyrano[2,3-c]acridine-7-ones 5-11 and their benzo [b]pyrano[2,3-h]acridine-7-one counterparts 12-18 were prepared by treatment of acronycine (1) or benzo[b]acronycine (4) with an excess of the appropriate dialkylaminoalkylamine. In both series, the introduction of a dialkylaminoalkylamino side chain at position 6 resulted in a significant increase of the cytotoxic activity against L1210 cells when compared with the parent compounds bearing a methoxy group, accompanied with an increased potency to arrest cells in the G2 + M phases of the cell cycle.

Publication types

  • Comparative Study

MeSH terms

  • Acridines / chemical synthesis*
  • Acridines / toxicity*
  • Acronine / analogs & derivatives
  • Acronine / chemical synthesis*
  • Acronine / toxicity*
  • Animals
  • Cell Division / drug effects
  • Cell Division / physiology
  • Drug Screening Assays, Antitumor / methods
  • Mice
  • Solubility
  • Tumor Cells, Cultured / drug effects
  • Tumor Cells, Cultured / physiology

Substances

  • Acridines
  • Acronine